Triacetoxyperiodinane → (5-Phenylisoxazol-3-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 70024Notes

Reaction equation

HRID 70024 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[OH:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 53364193(5-Phenylisoxazol-3-yl)(3,4,5-trimethoxyphenyl)methanol

Product 1

HCID 53364127(5-Phenylisoxazol-3-yl)(3,4,5-trimethoxyphenyl)methanoneYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 40i (0.110 g, 0.73 mmoL) in 8 mL anhydrous CH2Cl2 was added Dess-Martin reagent (0.274 g, 0.645 mmol). The mixture was allowed to stir for 30 min and quenched with sat. Na2S2O3 solution, extracted with ethyl acetate and dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to give pure compound 1i (70.1%). NMR (CDCl3) δ 7.87-7.85 (m, 2H); 7.72 (s, 2H), 7.53-7.49 (m, 3H), 7.05 (s, 1H), 7.82 (d, 1H, J=1.5 Hz), 3.97 (s, 3H), 3.96 (s, 6H); MS (ESI) m/z 362.1 (M+H)+.

Workup

  1. customquenched with sat. Na2S2O3 solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a70f0bf9c80d41c098d56675f32214ab
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

Loading…